2.0 2012-05-31 14:23:32 -0600 2015-06-03 17:19:09 -0600 ECMDB20025 M2MDB000874 1-Nitro-5-hydroxy-6-glutathionyl-5,6-dihydronaphthalene 1-nitro-5-hydroxy-6-glutathionyl-5,6-dihydronaphthalene belongs to the class of Peptides. These are compounds containing an amide derived from two or more amino carboxylic acid molecules (the same or different) by formation of a covalent bond from the carbonyl carbon of one to the nitrogen atom of another. (inferred from compound structure) (2S)-2-amino-5-(2R)-1-(carboxymethylamino)-3-(1-Hydroxy-5-nitro-1,2-dihydronaphthalen-2-yl)sulfanyl-1-oxopropan-2-ylamino-5-oxopentanoate (2S)-2-amino-5-(2R)-1-(carboxymethylamino)-3-(1-hydroxy-5-nitro-1,2-dihydronaphthalen-2-yl)sulfanyl-1-oxopropan-2-ylamino-5-oxopentanoic acid (2S)-2-amino-5-(2R)-1-(carboxymethylamino)-3-(1-Hydroxy-5-nitro-1,2-dihydronaphthalen-2-yl)sulphanyl-1-oxopropan-2-ylamino-5-oxopentanoate (2S)-2-amino-5-(2R)-1-(carboxymethylamino)-3-(1-Hydroxy-5-nitro-1,2-dihydronaphthalen-2-yl)sulphanyl-1-oxopropan-2-ylamino-5-oxopentanoic acid L-g-Glutamyl-S-(1-hydroxy-5-nitro-1,2-dihydro-2-naphthalenyl)-L-cysteinylglycine L-gamma-Glutamyl-S-(1-hydroxy-5-nitro-1,2-dihydro-2-naphthalenyl)-L-cysteinylglycine L-γ-Glutamyl-S-(1-hydroxy-5-nitro-1,2-dihydro-2-naphthalenyl)-L-cysteinylglycine C20H24N4O9S 496.491 496.126399076 (2S)-2-amino-4-{[(1R)-1-[(carboxymethyl)-C-hydroxycarbonimidoyl]-2-[(1-hydroxy-5-nitro-1,2-dihydronaphthalen-2-yl)sulfanyl]ethyl]-C-hydroxycarbonimidoyl}butanoic acid (2S)-2-amino-4-{[(1R)-1-(carboxymethyl-C-hydroxycarbonimidoyl)-2-[(1-hydroxy-5-nitro-1,2-dihydronaphthalen-2-yl)sulfanyl]ethyl]-C-hydroxycarbonimidoyl}butanoic acid [H][C@](N)(CCC(O)=N[C@@]([H])(CSC1([H])C=CC2=C(C=CC=C2N(=O)=O)C1([H])O)C(O)=NCC(O)=O)C(O)=O InChI=1S/C20H24N4O9S/c21-12(20(30)31)5-7-16(25)23-13(19(29)22-8-17(26)27)9-34-15-6-4-10-11(18(15)28)2-1-3-14(10)24(32)33/h1-4,6,12-13,15,18,28H,5,7-9,21H2,(H,22,29)(H,23,25)(H,26,27)(H,30,31)/t12-,13-,15?,18?/m0/s1 SFJZEQDXMXSLGC-RJXQQRCHSA-N Cytoplasm Periplasm logp -1.44 ALOGPS logs -4.04 ALOGPS solubility 4.48e-02 g/l ALOGPS logp -1.7 ChemAxon pka_strongest_acidic 1.83 ChemAxon pka_strongest_basic 9.54 ChemAxon iupac (2S)-2-amino-4-{[(1R)-1-[(carboxymethyl)-C-hydroxycarbonimidoyl]-2-[(1-hydroxy-5-nitro-1,2-dihydronaphthalen-2-yl)sulfanyl]ethyl]-C-hydroxycarbonimidoyl}butanoic acid ChemAxon average_mass 496.491 ChemAxon mono_mass 496.126399076 ChemAxon smiles [H][C@](N)(CCC(O)=N[C@@]([H])(CSC1([H])C=CC2=C(C=CC=C2N(=O)=O)C1([H])O)C(O)=NCC(O)=O)C(O)=O ChemAxon formula C20H24N4O9S ChemAxon inchi InChI=1S/C20H24N4O9S/c21-12(20(30)31)5-7-16(25)23-13(19(29)22-8-17(26)27)9-34-15-6-4-10-11(18(15)28)2-1-3-14(10)24(32)33/h1-4,6,12-13,15,18,28H,5,7-9,21H2,(H,22,29)(H,23,25)(H,26,27)(H,30,31)/t12-,13-,15?,18?/m0/s1 ChemAxon inchikey SFJZEQDXMXSLGC-RJXQQRCHSA-N ChemAxon polar_surface_area 231.85 ChemAxon refractivity 121.43 ChemAxon polarizability 47.19 ChemAxon rotatable_bond_count 12 ChemAxon acceptor_count 12 ChemAxon donor_count 6 ChemAxon physiological_charge -2 ChemAxon formal_charge 0 ChemAxon glutathione metabolism II The biosynthesis of glutathione starts with the introduction of L-glutamic acid through either a glutamate:sodium symporter, glutamate / aspartate : H+ symporter GltP or a glutamate / aspartate ABC transporter. Once in the cytoplasm, L-glutamice acid reacts with L-cysteine through an ATP glutamate-cysteine ligase resulting in gamma-glutamylcysteine. This compound reacts which Glycine through an ATP driven glutathione synthetase thus catabolizing Glutathione. This compound is metabolized through a spontaneous reaction with an oxidized glutaredoxin resulting in a reduced glutaredoxin and an oxidized glutathione. This compound is reduced by a NADPH glutathione reductase resulting in a glutathione. Glutathione can then be degraded into various different glutathione containg compounds by reacting with a napthalene through a glutathione S-transferase PW001927 Metabolic Specdb::CMs 37175 Specdb::CMs 48135 Specdb::CMs 136599 Specdb::CMs 144333 Specdb::CMs 167466 Specdb::CMs 167468 Specdb::CMs 167470 Specdb::CMs 167472 Specdb::CMs 167474 Specdb::CMs 280608 Specdb::NmrOneD 57212 Specdb::NmrOneD 57213 Specdb::NmrOneD 57214 Specdb::NmrOneD 57215 Specdb::NmrOneD 57216 Specdb::NmrOneD 57217 Specdb::NmrOneD 57218 Specdb::NmrOneD 57219 Specdb::NmrOneD 57220 Specdb::NmrOneD 57221 Specdb::NmrOneD 57222 Specdb::NmrOneD 57223 Specdb::NmrOneD 57224 Specdb::NmrOneD 57225 Specdb::NmrOneD 57226 Specdb::NmrOneD 57227 Specdb::NmrOneD 57228 Specdb::NmrOneD 57229 Specdb::NmrOneD 57230 Specdb::NmrOneD 57231 Specdb::MsMs 29120 Specdb::MsMs 29121 Specdb::MsMs 29122 Specdb::MsMs 35678 Specdb::MsMs 35679 Specdb::MsMs 35680 11954056 10128351 C14805 Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. 22080510 Glutathione S-transferase P0A9D2 GST_ECOLI gst http://ecmdb.ca/proteins/P0A9D2.xml GSH-dependent disulfide bond oxidoreductase P77526 yfcG http://ecmdb.ca/proteins/P77526.xml 1-Nitronaphthalene-5,6-oxide + Glutathione <> 1-Nitro-5-hydroxy-6-glutathionyl-5,6-dihydronaphthalene R07025 1-Nitronaphthalene-5,6-oxide + Glutathione > 1-Nitro-5-hydroxy-6-glutathionyl-5,6-dihydronaphthalene PW_R005409